A kayaker in a turquoise sea near a rocky cliff.

Holiday Homes in Midland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Midland holiday homes

A house with a blue door and a wooden deck.

1. The Little Lake House-Cozy 2Bdrm

The Little Lake House-Cozy 2Bdrm
Midland
8.8 out of 10, Excellent, (6 reviews)
"Excellent!!"
Canada
Alana B.
The price is €223
includes taxes & fees
16 Sept - 17 Sept
The Little Lake House-Cozy 2Bdrm
A wooden boardwalk through a natural area with dense vegetation and a clear sky.

2. Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage

Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
Victoria Harbour
8.4 out of 10, Very good, (27 reviews)
"The place has everything you need for comfortable stay with clean big rooms and supplies. It is an Old Place with spacious and ample rooms. Doors needs some greasing and it would also help to have some light in the yard for evening. Overall experience was great."
Canada
Akhila
The price is €266
includes taxes & fees
9 Sept - 10 Sept
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage

3. Lovely & cozy private vacation home/Cottage 3 min. walk to Beach 2

Lovely & cozy private vacation home/Cottage 3 min. walk to Beach 2
Wasaga Beach
9.0 out of 10, Wonderful, (2 reviews)
"Good location, clean inside, but behind the building was much stink door because they had put some bags of old food garbage inside the garage!"
Canada
Anoush P.
The price is €269
includes taxes & fees
13 Sept - 14 Sept
Lovely & cozy private vacation home/Cottage 3 min. walk to Beach 2
A cabin with a sloped roof, large windows, and a wooden deck.

4. A-Frame Escape in the Woods of Georgian Bay, Muskoka

A-Frame Escape in the Woods of Georgian Bay, Muskoka
Georgian Bay
10.0 out of 10, Exceptional, (6 reviews)
"Loved this place! Beds were comfortable, it had everything we needed, nice and private, everything was so clean and we loved the sauna! Would absolutely stay here again. "
Canada
Kimberly S.
The price is €479
includes taxes & fees
21 Sept - 22 Sept
A-Frame Escape in the Woods of Georgian Bay, Muskoka
A swimming pool with inflatable toys, surrounded by a stone wall and greenery.

5. Lost in Hillsdale | 10 mins to Horseshoe Valley

Lost in Hillsdale | 10 mins to Horseshoe Valley
Hillsdale
9.0 out of 10, Wonderful, (2 reviews)
"Excellent accoms, as pictured, close to the slopes, would re-book & reco"
Canada
Elvira K.
The price is €421
includes taxes & fees
15 Sept - 16 Sept
Lost in Hillsdale | 10 mins to Horseshoe Valley
A modern apartment with a kitchen, dining area, and a balcony with railings.

6. Stunning Muskoka Oak Bay Golf Course - Port Severn Townhouse sleeps 8 free wifi

Stunning Muskoka Oak Bay Golf Course - Port Severn Townhouse sleeps 8 free wifi
Port Severn
10.0 out of 10, Exceptional, (1 review)
"Amazing house in a awesome location ! Couldn't have asked for better :)Jennifer was a great host and provided us with everything we needed ... and more !!!"
Canada
Dominique T.
The price is €793
includes taxes & fees
8 Sept - 9 Sept
Stunning Muskoka Oak Bay Golf Course - Port Severn Townhouse sleeps 8 free wifi
A wooden deck leading to a house with a star decoration, a white door, and a window.

7. Moonstone Cottage/ Ski Retreat

Moonstone Cottage/ Ski Retreat
Oro-Medonte
8.0 out of 10, Very good, (1 review)
The price is €296
includes taxes & fees
22 Sept - 23 Sept
Moonstone Cottage/ Ski Retreat
A modern kitchen with granite countertops, a dining area with blue chairs, and a living space with a TV and hanging chair.

8. House in Wasaga only 18 min away from Blue Mountain! 5 min away from the beach!

House in Wasaga only 18 min away from Blue Mountain! 5 min away from the beach!
Wasaga Beach
10.0 out of 10, Exceptional, (7 reviews)
"Nice location and clean, refreshing, and relaxing atmosphere. Very spacious, even with many people. Very responsive and helpful owner."
Canada
Jamie F.
The price is €365
includes taxes & fees
8 Sept - 9 Sept
House in Wasaga only 18 min away from Blue Mountain! 5 min away from the beach!
A beach with people walking along the shore, a clear sky, and buildings in the background.

9. Entire Bungalow in Wasaga Beach ⛱️

Entire Bungalow in Wasaga Beach ⛱️
Wasaga Beach
9.2 out of 10, Wonderful, (10 reviews)
"We were a group of 11 friends who stayed here for a couple of days while we skied in Collingwood. The house was clean and exactly as described. Plenty of beds for our group. Communication with the host was really good and he allowed us to check in early. "
Canada
Caden T.
Entire Bungalow in Wasaga Beach ⛱️
A modern kitchen with a central island, stainless steel appliances, and a dining area with glass-top table and cushioned chairs.

10. Clearview Manor (Wasaga Beach)(Blue Mountain)

Clearview Manor (Wasaga Beach)(Blue Mountain)
New Lowell
8.0 out of 10, Very good, (2 reviews)
"It’s a nice property and has plenty of room for everyone however for what they charged, I would book somewhere else. This place was renovated by someone who has no clue what they are doing, as you can see in the pictures (and it’s everywhere in the house) I also didn’t like how it says it sleeps 30 but they charge you extra after 10 or so people. This should be clear in big writing. Almost 900 in extra charges for the 21 guests we had. "
Canada
Chris Z.
The price is €1,177
includes taxes & fees
8 Sept - 9 Sept
Clearview Manor (Wasaga Beach)(Blue Mountain)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Midland Hotel Reviews

Carriage Ridge Resort, an Ascend Collection Resort

Carriage Ridge Resort, an Ascend Collection Resort

10/10 Excellent
"Amazing experience and great area, highly recommended!"
Bence 1-night trip
Posted 13 hours ago
Carriage Ridge Resort, an Ascend Collection Resort

Find out more about Midland

Midland Holiday Homes information

Number of reviews
5,132
Accommodation
135 Holiday Homes
Lowest Price
€56
Highest Price
€298